Literature DB >> 21627306

Novel application of α-azido aldehydes in multicomponent reactions: synthesis of triazolo-fused dihydrooxazinones via a Passerini reaction-dipolar cycloaddition strategy.

Fabio De Moliner1, Stefano Crosignani, Andrea Galatini, Renata Riva, Andrea Basso.   

Abstract

α-Azido aldehydes can be employed in Passerini reactions with isocyanides and various propiolic acids to afford the three-component adducts in moderate to good yields. These compounds undergo a straightforward azide-alkyne dipolar cycloaddition to furnish triazolo-fused dihydrooxazinones.

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Year:  2011        PMID: 21627306     DOI: 10.1021/co200072z

Source DB:  PubMed          Journal:  ACS Comb Sci        ISSN: 2156-8944            Impact factor:   3.784


  7 in total

1.  Synthesis of trans-1,3-diaryl-2-(5-methylisoxazol-3-yl)-2,3-dihydro-1H-naphtho[1,2-e][1,3]oxazines via bismuth(III)-catalyzed one-pot pseudo-four component reaction.

Authors:  Mehdi Shafiee; Ahmad Reza Khosropour; Iraj Mohammadpoor-Baltork; Majid Moghadam; Shahram Tangestaninejad; Valiollah Mirkhani; Hamid Reza Khavasi
Journal:  Mol Divers       Date:  2012-10-23       Impact factor: 2.943

2.  One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles.

Authors:  Wei-Shun Hsu; Vijaykumar Paike; Chung-Ming Sun
Journal:  Mol Divers       Date:  2013-03-26       Impact factor: 2.943

3.  Aldol reactions in multicomponent reaction based domino pathways: a multipurpose enabling tool in heterocyclic chemistry.

Authors:  Zhigang Xu; Fabio De Moliner; Alexandra P Cappelli; Christopher Hulme
Journal:  Org Lett       Date:  2013-05-29       Impact factor: 6.005

4.  Synthesis of triazolo-fused benzoxazepines and benzoxazepinones via Passerini reactions followed by 1,3-dipolar cycloadditions.

Authors:  Fabio De Moliner; Martina Bigatti; Chiara De Rosa; Luca Banfi; Renata Riva; Andrea Basso
Journal:  Mol Divers       Date:  2014-06-04       Impact factor: 2.943

5.  Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols.

Authors:  Miao An; Wanyi Liu; Xiaoying Zhou; Ran Ma; Huihui Wang; Baodong Cui; Wenyong Han; Nanwei Wan; Yongzheng Chen
Journal:  RSC Adv       Date:  2019-05-24       Impact factor: 3.361

Review 6.  Diversity oriented syntheses of conventional heterocycles by smart multi component reactions (MCRs) of the last decade.

Authors:  Heiner Eckert
Journal:  Molecules       Date:  2012-01-20       Impact factor: 4.411

Review 7.  The 100 facets of the Passerini reaction.

Authors:  Luca Banfi; Andrea Basso; Chiara Lambruschini; Lisa Moni; Renata Riva
Journal:  Chem Sci       Date:  2021-09-30       Impact factor: 9.825

  7 in total

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